Air Force One will touch down on Cuban soil for the first time ever on Sunday but what happens next is anyone’s guess.

That's largely because President Barack Obama will be the first sitting U.S. commander in chief to visit the island nation in almost 90 years. How Cuban leaders and citizens will respond when he arrives with dozens of business-minded American lawmakers and CEOs in tow is anyone's guess.

Obama’s goals for the historic visit are to “deepen relations” and bring about “more effective business ties,” White House Press Secretary Josh Earnest said Friday. But “I don’t think our goals are only economic,” he said, adding Obama intends to send a message to all concerned that America is in the midst of normalizing relations with a former enemy. Much attention will focus on the response to Obama standing side-by-side with President Raul Castro on Cuban soil. Also sure to get ample attention: how the American contingent's clear desire to open the Caribbean country to the U.S. agriculture, hospitality and other industries will sit with Cubans.

“In terms of the policy, the idea is to help to try to engineer a soft landing in Cuba, which avoids violence and civil strife in Cuba or a major immigration crisis of people fleeing an unsettled domestic political situation,” Richard Feinberg, a former special assistant for national security affairs to President Bill Clinton, said during a recent event at the Brookings Institution.

“The idea is to promote a gradual incremental transition to a more open, pluralistic and prosperous Cuba integrated into global markets of goods, capital and ideas. It is a long-term strategy,” said Feinberg, now a non-resident senior fellow at Brookings. “It cannot be measured by quarterly reports.”

Here are four things to watch as Obama’s latest long-term foreign play begin to come into focus:

1. Obama and Castro

Obama’s one full day in Cuba, Monday, will put the brother of longtime Cuban leader Fidel Castro on center stage. He'll play host at the former presidential palace in Havana.

The leaders will no doubt be all smiles when they pose for pictures and possibly give statements following a closed-door meeting. But the White House has made clear Obama likely will at least remind Castro that Washington expects his government to do more to remedy a list of human rights abuses.

To that end, Earnest acknowledged to reporters Friday that the Castro regime has fallen short of making the kinds of strides Washington and other countries have desired. What’s more, Obama is slated to meet with a group of Cuban political dissidents whose identities the White House is holding close.

“From the Cuban perspective, there is a big risk in this visit,” Feinberg said. “Although Raul and Barack Obama will shake hands and smile, in fact, between the two of them, there is a battle of symbol and ideas.”

2. Getting Down to Business

Though the House is seeking to dispel notions that the visit is mostly about strengthening economic ties, it is agenda item No. 1.

The Marriott hotel corporation’s CEO will be there, as well as other titans of American industry. The White House expects “several dozen members of Congress” will make the journey south, many from agriculture-rich states eager to connect with a new market.

For members like Democratic Sen. Heidi Heitkamp of North Dakota, Obama's trip represents a potential shot in the arm for farmers. And, like the White House, they see it as a bargaining chip in Washington’s efforts to force the Castro regime to address issues that irk the West.

Also on Monday, Obama will attend an event with Cuban entrepreneurs. And the administration sees a clear linkage between improved U.S.-Cuban economic ties and the empowerment of everyday citizens.

“This is a sector of the Cuban economy and society that holds enormous promise in improving the livelihoods of the Cuban people,” Rhodes said. “And more broadly, the commercial opening between our countries similarly has the potential to be a truly mutual interest in terms of providing opportunities -- not just for U.S. businesses -- but opportunities that … help empower and improve the lives of Cubans.”

3. Garland Nomination Momentum

The timing of the trip raises questions about whether Obama and his team can maintain pressure on Senate Republicans to consider Merrick Garland’s Supreme Court nomination -- and keep public attention on GOP leaders' vows not to hold hearings or allow an up-or-down vote.

“The president will continue to be engaged in this process” Earnest said Thursday when asked how the administration will multitask.

“There will be one or two opportunities over the course of the five-day trip for the president to take questions from all of you,” Earnest told reporters. “So to the extent that all of you may continue to be interested in this story, maybe you'll have some questions for the president.”

4. That Other Stop

For historical reasons, the Cuba stop of Obama’s five-day trip is getting the most attention. But the president will not simply fly from Havana to Washington on Tuesday evening. Instead, he’ll head to Argentina.

Susan Rice, Obama’s national security adviser, called it “another visit that would have seemed unlikely not long ago.” She also said White House officials “believe this trip will be an historic and powerful demonstration of our nation’s new approach to Latin America -- an approach that will guide us for the remainder of the Obama administration.”

The White House is expected to use the president’s final-year trips to underscore the merits of engaging -- rather than isolating or punishing -- countries that could be U.S. partners if it were not for handful of disputes. Argentina falls into that category.

Argentina’s secretary of trade, Miguel Braun, recently declared Argentina “open for business.” The administration is eager to cash in on its efforts to engage Argentine leaders. “We’re keen to expand our economic relationship,” Rice said this week.

Though Obama and Argentine President Mauricio Macri will get down to business, the White House wants to see more changes. “We expect that President Obama and President Macri will announce a number of new partnerships,” Rice said, “including efforts to combat crime and drug trafficking, promote sustainable energy development, and fight climate change.”